To try and impose some discipline on myself, I rented some office space, and would go there every day. But with the rest of my company, and most of my clients, asleep until about 1pm UK time, I would usually sleep in. I might go to the gym first thing, and get to the office around 10am, where I’d basically browse Reddit and listen to podcasts until about 1pm, when everyone would wake up and start posting on Slack, which is when I’d get to work. I would also finish working around 6pm, when my girlfriend got home from work. I was basically working 5 hours a day. In many jobs, this would be enough to get everything done. But in a fast-growing startup. I was struggling to keep up, because it just wasn’t enough time to get all my work done. The other issue is that working remotely is lonely, especially when most of your company isn’t awake until halfway through your working day. There’s a lot less banter and talk between colleagues, even with tools like Slack. Some people don’t need that interaction, and like the peace and quiet that comes from working at home. I’m not one of those people. I’m naturally an extrovert, and I need the daily interaction and the energy it gives me. There’s no substitute for having people sat next to you that you can talk to, or having your colleagues sat next to you working hard, and making you feel like you should be doing the same. And when you’re working remotely, it’s a lot easier to ignore a problem. I didn’t take ownership for the issues that I noticed or that were under my control. In fact, I didn’t take ownership for myself: for my own productivity and work habits. I let myself be a victim to my circumstances, instead of doing the hard work to fix it. 2. I am too eager to please people, and I don’t like confrontation. I said that a big part of my job was solving issues for our clients. Unfortunately, these problems were sometimes partly out of my control — for example, if we were waiting on some book cover designers from a freelance designer. I was usually too eager to please the client, so I’d give them unrealistically short timeframes for when we’d have the designs back. That date would come and go, and the client would follow up with me, annoyed. Rather than deal with that issue, I’d just ignore it, and not answer their email. This happened multiple times, and as you can imagine, this is really bad customer service. But seeing as though I was the client’s only point of contact, there was no-one for them to complain to–so I could get away with it. At least for awhile. I was struggling to keep up, because the company was growing so fast, and I was the only one dealing with all of our clients. We could have hired more people to help me. But I didn’t say anything to Tucker or Zach about it for a long time, for a couple of reasons: I felt guilty about not working hard enough, because I knew the problem was partly my fault; and I didn’t want to complain and make it sound like I was causing problems. I was too eager to keep them happy, and just decided to suffer in silence, rather than raise the issue and have a difficult conversation (for me) about how to solve the problem. This actually had a really harmful effect: I kept expecting to be “found out”, so I would put off opening up my emails or Slack in the morning, because I was always convinced that today would be the day someone would realise I suck at my job, and there’d be an angry message waiting for me, telling me how bad I was. And this anxiety meant that I dreaded opening up my laptop every day. I buried my head in the sand, and refused to face the issue. Which, of course, only made things worse. 3. I am sometimes humble — to a fault. I’m a smart guy, but I’m well aware that I don’t have the answer to everything. And having followed Tucker’s career and looked up to him for a long time, I knew he was extremely smart, and a good entrepreneur. But I looked up to him too much, and often substituted his judgement for my own. I remember one occasion where we were talking about when we’d need to hire someone else to do the same thing as me — how many clients we’d need to get before I would reach breaking point. I thought the answer would be about 50. Tucker thought it was more like 100. What I should have said was: “Tucker, I think you’re wrong — here are the issues with what your estimate, and here’s why my answer is more likely to be right — and if I do need to be able to handle 100 clients, here are the problems we need to solve to get there.” What I actually said was…nothing. Instead, I thought to myself, “OK, Tucker’s smarter than me, so he must be right about this — even though I’m the only one doing this job and have a lot more information about it than he does, and he has a habit of anchoring to high expectations. He’s probably right.”